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<h1><a href="https://archiveofourown.org/works/24982792">Roleplay Jensen Style</a> by <a class='authorlink' href='https://archiveofourown.org/users/Misshyen/pseuds/Misshyen'>Misshyen</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>Jensen and Claire:  A Loser's Humorous Love Story [39]</td></tr>

<tr><td><b>Category:</b></td><td>Jake Jensen - Fandom, The Losers, The Losers (2010)</td></tr>

<tr><td><b>Genre:</b></td><td>F/M, Fluff and Humor, Jake Jensen fanfiction, Jensen and ofc, Orgasm, Role Playing, Roleplay, Sexual Roleplay, Sexy role play, handjob, jensen fanfiction, loving couple, the losers fanfiction</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-06-29</td></tr>

<tr><td><b>Updated:</b></td><td>2020-06-29</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-04 02:02:30</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>3,610</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/24982792</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/Misshyen/pseuds/Misshyen</td></tr>

<tr><td><b>Relationships:</b></td><td>Jake Jensen &amp; Original Female Character(s)</td></tr>

<tr><td><b>Series:</b></td><td>Jensen and Claire:  A Loser's Humorous Love Story [39]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/620515</td></tr>

<tr><td><b>Comments:</b></td><td>8</td></tr>

<tr><td><b>Kudos:</b></td><td>17</td></tr>

</table>

<a name="section0001"><h2>Roleplay Jensen Style</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>Late one Friday evening after they had finished dinner and were sitting and finally relaxing together, Jake was casually fiddling with a small technical gadget as Claire watched a sitcom next to him.  He kept looking over at her grinning, chuckling to himself which caused her to glance over occasionally and give him questioning looks.  Eventually he put his gadget down and turned to face her with a goofy smile.</p><p>“Love of my life?”  By his tone of voice, Claire knew something mischievous or flirty was about to be asked.  She looked at him and smiled with her brows raised, waiting for the question.</p><p>“Uh oh.”  She smiled, “I sense something crazy coming.”</p><p>“No, no uh ohs.”  He laughed as he scooted closer to her.</p><p>“Well when you call me love of your life you usually have something goofy to tell me.”  She reminded him, still waiting to hear what he had to say.</p><p>“Sometimes maybe, but this time I have an idea.”</p><p>“Uh oh.”  She repeated, letting out a giggle as he moved positions on the couch, flopping down and resting his head on her lap, looking up at her.</p><p>“Okay so how cool are you with the idea of roleplaying?”  He waited expectantly for her answer, adjusting his glasses.</p><p>“As in cosplay at conventions or the sexy kind?”  She looked down at him hesitantly, watching his large puppy eyes stare up at her.</p><p>“Yeah the hot kind, like you could be a sexy massage therapist and I come in for a massage and then I can’t pay you so I have to offer you sexual favors.”</p><p>Claire laughed, running her fingers in his short hair.  “First of all, I already<em> am</em> a massage therapist.  I thought role-play is something you pretend to be for kicks.”</p><p>“I’ve role-played in my uniform before.”  Jake debated.</p><p>“I didn’t think that was role-play as much as it was just you fulfilling a desire of mine.  Plus, what about pirate Jake and the tavern wench.”</p><p>Jake scrunched his nose and made a face, “Ah shit, you’re right.”  He rubbed an eye under his glasses and looked at the ceiling thoughtfully.  “Well I meant what if we did that kind of stuff more often.”</p><p>“Ahhhh I see where this is going now.”  She leaned down to kiss him quickly and grinned, “I will do anything you want if it makes you happy.  So long as I’m not just a sexy cliché librarian or nurse.”</p><p>“Ha sucker, I knew you’d go for it!  I get to pick the first costume and you’ll love it!”</p><p>She let out a belly laugh, “You called me sucker because I agreed?”  Continuing to play with his hair she smiled.  “Is the costume for me or you?”  She asked warily, running her other hand up under his t shirt and scratched along his tight lightly haired abdomen.  She swore she heard him let out a purr and scratched a little harder.</p><p>“For me because I know exactly what I’m going to do.”  He looked pleased like a little boy getting a treat and Claire smiled down at him as she rolled her eyes.</p><p>“Why do I have a feeling this is going to be taken waaay out of proportion?”  She knew how much Jake loved to make her laugh and she could tell he had some plans up his sleeve while attempting to be intimate.</p><p>“Nah, it’s not like that, I promise you.” He assured her.</p><p>“Hmm, we’ll see.  This is you and you like to go in guns blazing on everything you do.”</p><p>Jake sat up and kissed her cheek before pulling her on to him so she was now lying with her head in his lap.  “You’ll see, it’ll be sexy and fun.”</p>
<hr/><p> </p><p>A week later she was running late coming home from work, stressed and her feet were sore.  When she walked in the door all she wanted was a hot shower and something to eat.  Work had been a madhouse and she wished at that moment she had her own massage happening.</p><p>She shut the front door and tossed her bag on the nearby table and heard merry whistling coming from the kitchen.  The smell of tomato sauce and hamburger cooking cause her mouth to water.  He wasn’t the best cook but Jake made a good spaghetti and meat sauce.  “Hey in there, whatcha cooking, it smells good in he—.”  She was heading to the kitchen and stopped in her tracks when she found Jake standing over the stove stirring something in a pan.  “Oh my God!  What are you doing??”</p><p>Jake stood naked with his bare ass peeping from a white apron the long ties resting down the crack of his ass. He had on black socks and was wearing a hair net while an unlit cigarette hung from his lips, threatening to drop into the food at any moment.  There was a slight day old beard shadow forming around his goatee which gave him an almost haggard look.  His bulk under the small white apron looked ridiculous, especially while naked.  She kept looking from his serious expression to the slight dip on the side of his toned butt cheeks and didn’t know if she was aroused by his naked rear and muscular thighs or horrified at the outfit.</p><p>“Cookin’ sloppy joes, hun.”  He grunted in a gruff voice, in character, as he turned off the stove.  He turned to Claire and stared at her as he gripped the spatula, his glasses resting halfway down his nose.  He expression was serious, and Claire expected him to break out of character into his boyish grin but nothing happened.</p><p>“What in the world are you doing??”  She repeated, her mouth opened in surprise, an eyebrow raised, not knowing whether to laugh or be disturbed.</p><p> “You told me you earlier you were having a bad day and how you just wanted me to make something for dinner, so Sexy Lunch Lady Jake is here to make you all better.”  He sauntered toward her lifting the apron a bit innocently flashing her as he wiped his hands finger by finger on the fabric.  She held up her hands defensively as she let out a shriek.</p><p>“No no no no, that’s not sexy!”  She started to laugh, a snort escaping as she lost control and let the laughter grow, “You couldn’t be a sexy short order cook?  You chose to be a sexy lunch lady!”</p><p>“What are you talkin’ ‘bout hun, you don’t want to give Lunch Lady Jake a kiss?”  The cigarette wobbled violently on his lower lip and then fell out of his mouth onto the floor as he spoke and Claire laughed harder causing a grin finally break on his face.  “Oops…”</p><p>She tried to run off as he lunged for her, grabbing her around the waist, “This is not sexy!  Put me down!”  She gasped as he tickled her ribcage carrying her to the living room.  “Put some clothes on, lunch lady!  You’re terrible at your job!”</p><p>“Come on!  It made you laugh didn’t it?”  He broke character and laughed with her as he set her down on the couch and stood in front of her, taking off his apron.  She stopped laughing and calmed down watching his naked physique as he stood smiling at her, holding the spatula still with a silly expression, wearing only socks and the hair net.</p><p>“Lunch ladies usually aren’t naked.”  She noted as she curled up on the couch and hugged a large pillow to her chest, wiping tears off her cheek “You’re fired!”</p><p>Jake let out an exaggerated sigh and tossed his arms in the air, “Fine, but you should know that I’m in the union.”  He started to walk away and Claire laughed harder at his toned ass bunching and relaxing as he headed to the stairs, “You’ll be hearing from my lawyer!”</p><p>“I don’t care as long as it’s not Sexy Lawyer Jake!”  She shouted toward the stairs, laughing.</p><p>“Party pooper!”  was Jake’s retort from the bedroom.</p>
<hr/><p> </p><p>A couple days later, Claire sat waiting on their bed as she heard Jake making all sorts of noises from the bathroom behind the closed door.  They had decided on a doctor and patient role-play that was cliché but something they could work with.</p><p>“I’m almost ready!  Just be patient, the doctor will see you in a moment!”  He called out to her.</p><p>Claire giggled and cringed as she heard a snapping sound of latex and then Jake cursing under his breath sounding pained.</p><p>“Are you okay in there?”  She asked slightly concerned, starting to get up to go to the door.  Jake flung the door open, and Claire let out a whoop of glee as he strode over to her in a white doctor coat, and a colorful plastic toy stethoscope over his shoulder.  He snapped the other glove on his wrist and yelped in pain.</p><p>“Shit!  Wrist hair…”</p><p>Claire put her hand on her hip and shook her head, “Wow.”  She looked him up and down and grinned, “Wow…”</p><p>“The doctor will see you now.”  Jake purred as he picked Claire up and carried her to the bed.  “You should be back in bed ma’am; you need your rest.”</p><p>“You’re very professional, doctor.  Tell me, where did you get such a fancy stethoscope.” She leaned up against the pillows as Jake set her down and climbed onto the bed over her, his knees resting on either side of her hips.</p><p>“That’s not important ma’am, right now we need to get you better.”  He started to lift Claire’s tank top and she looked down and noticed the gap between his jacket and his bare chest.  She undid the jacket and opened it to find blue boxers with stethoscopes and thermometers all over them.  Jake leaned up and took the jacket off and then lowered himself over her again.  He began to kiss her neck and Claire wrapped her arms around his neck with a satisfied hum.</p><p>She was quiet for a moment before she remembered his gloves and boxers and started to laugh.</p><p>“Ma’am please, this is serious.  I’m trying to check your pulse.”  Jake resumed kissing her neck and Claire grinned.</p><p>“With your lips?  Oh doctor…”  She held onto him tighter and pulled him closer.  After a moment she started to giggle again quietly, her body shaking with glee.</p><p>Jake sat up and sighed impatiently, “Claire…”</p><p>“I’m sorry, but the boxers and you snapping your gloves along with the toy stethoscope crack me up.  You look so cute!”</p><p>Jake frowned slightly and sighed, “I’m not cute, I’m sexy doctor Jake, I have an MD-PHD in being sexy.”  He put his hands on his hips as he knelt over her, “You said you’d try anything, so come on, no more giggles.”</p><p>Claire noted his expression and nodded, biting back a smile, “I’m sorry doctor, this <em>is</em> serious.”  She leaned up on her elbows and looked up at Jake with a mock pout giving him bedroom eyes, “Doctor, can you help me, I have a pain in my wrist.”</p><p>Jake’s eyes widened and he grinned happily, “Oh do you?  Well here”, he took her hand and guided it to his semi erection.  “Hold this and I want you to really grip it.  We have to see how hurt your wrist is.  You’re going to have to really stroke so I can see just how injured your wrist is.”</p><p>Claire nodded, biting her lips together and ran her hand along him.  He leaned closer and rested his head on hers with a soft sigh and moan.</p><p>“So how is my wrist doctor?”  She asked softly.</p><p>“I uh… seems okay but... not convinced…”  He began to thrust against her hand letting out a small whine of need.  “Fuck that feels good.”</p><p>She looked down to reach into the pocket of his boxers and noticed the pattern again starting to giggle once more.  She let out a soft snort as her laughter grew again and he sighed.</p><p>“Claire, come on.”  He groaned.</p><p>“I’m sorry, it’s just the boxers, they’re so cute!”  She pouted sympathetically face as Jake moved away.  “Wait come back, take them off, they’re just a little distracting.”</p><p>Jake sighed and stood up, shucking off the boxers before sitting on the edge of the bed, “Better?”</p><p>Claire nodded and held up her wrist, “Okay, so anyway doctor, my wrist is still sore.”</p><p>Jake took her wrist gently and kissed it, “Well let’s see here ma’am.  I see the problem and I think I can help.  He bent over her and his lips met hers softly brushing along them for a few minutes before sitting back up again.  Claire started to giggle again and Jake gave a disapproving hum.  As he sat back.  “But before we begin, do you have insurance?”</p><p>She was caught off guard and looked at him questioningly, “Do I what?”</p><p>“Do you have insurance?”  He repeated, his voice not sounding like normal silly Jake.</p><p>“Oh um, this is weird role play, but no.  I thought I could repay you in certain favors.”  She moved to her side with a seductive smile and ran her hand along his thigh, moving further between his legs.</p><p>Jake stood up swiftly and picked up his boxers and jacket, “Ok well then I’m sorry but I can’t see you.”  He walked to the bathroom.  “Please see the receptionist on the way out.”</p><p>Claire sat up quickly, “Wait what??”  She cocked her head to the side, confused.  “Are you serious?”</p><p>Jake peeked out of the bathroom again, “The doctor is away and I’m not in the mood anymore.  Good day madam.”</p><p>“Jake wait, I’m sorry, I won’t giggle anymore.”</p><p>“I said good day!”</p><p>“Aw come on sweetie.”  Claire sat up looking perplexed at the bathroom door.  She looked at the floor and noticed the toy stethoscope and bit her lips together to stop from laughing again.</p>
<hr/><p> </p><p>One weekend afternoon, she was sitting at the dining room table eating a snack and reading a magazine when she heard boots clomping down the stairs.  She perked up with an idea and a grin.</p><p>“Hey, you want to go hit up the outlets with me?  I’ll get you a pretzel after.”  She looked up and saw Jake enter the room with his pirate hat on, black boxers with skull and crossbones all over them and black boots.</p><p>“Oh well hello there, Pirate Jake.”  She looked up at him and her mouth dropped open a bit, Pirate Jake was her favorite role play by far and she was ready to leap the table to get to him almost drooling.</p><p>“Shush, miss.”  Jake growled, his voice low and stern.</p><p>Claire gave him a surprised look and stood up.  “What if I don’t?  You don’t give me orders.”  She replied with sass and she strode over to him and traced her fingers up his chest.  Jake looked down at her hands and then back into her eyes.</p><p>“Did I say you could touch me?”  He snarled.</p><p>“No captain.”  She wiggled with impatience as she pulled her hands away.  Grabbing her upper arms firmly but keeping his grip in check, her stared her down, getting into the role quickly.  He had learned a while ago that he could be rougher while in character and she loved it, always encouraging more.  He was never violent but he would hold her tighter, give more demanding orders, and she was more than welcoming to it all.  They had long ago established boundaries and along with love and trust, Pirate Jake and tavern wench Claire were always a fun sexual favorite with them.</p><p>She let out a soft involuntary groan and stood still waiting for his next move, “Captain, are you going to have me again like that night above the tavern?”  She leaned over and kissed him, “I miss you while you’re at sea, no other man could ever satisfy me the way you can.”</p><p>Jake grabbed around her waist and pulled her closer to him, her breast crushed against his chest.  “Of course they couldn’t.”</p><p>She fidgeted uncomfortably and kissed Jake’s nose before stepping back, “Hold that thought.”  She scrambled out of Jake’s grip and trotted out of the room.</p><p>“Where are you going?”  Jake watched, breaking character.</p><p>“Gotta pee first, be right back!”  She called back.</p><p>“Oh my God Claire you are the worst role player!”  He laughed as he crossed his arms and stood in the dining room waiting.  After a moment she came back in the room, rubbing her hands on her jeans.</p><p>“Okay, please continue now, Captain Impatience.</p><p>“Are you sure?”  Jake asked with a raised eyebrow.</p><p>“Yes, I’m ready to go.”  She stepped over to Jake and put his arm around her waist again resuming their earlier position.  “So Captain—”</p><p>“Quiet Miss, I’ve been at sea too long to hear you talk.  Get your clothes off.”  He stood back as Claire eagerly reached for the hem of her shirt pulling it off slowly, her bare breasts bounced slightly as they came loose from her shirt and Jake let out a breath.</p><p>“Shit.”  He whispered, grabbing himself and holding tight for a moment.  She took off her jeans and panties, kicking them to the side and standing before him naked.</p><p>“Jesus you are so gorgeous.”  Jake muttered as he grabbed for her again, pulling her into his arms.  He slid his palm down to her ass and slapped it smartly causing Claire to yelp.</p><p>“Miss this, Captain?”  She teased.</p><p>“Aye.”  He murmured gruffly, lowering his mouth to her breast, holding it in a large hand, lapping and tugging at a nipple eagerly.  He let go of her long enough to yank his boxers off roughly, his dick springing up against Claire’s thigh.</p><p>“Captain!”  She gasped, “So eager!”</p><p>“Hush lass.”  He warned, “I want to fuck, eat a hot meal and have my ale.  Then fuck you again before I fall asleep in your beautiful arms.”</p><p>“Oh my, aren’t you bossy this visit.”  She wrapped her hand around his neck and kissed him urgently, small groans escaping their throats.  “I think I can help with that.”</p><p>He stood back up and looked down at her.  “Since we’re on my ship, it’s a shame I have to punish you for your sassy behavior.”  He gestured under the dining room table, “Get into the brig.”</p><p>“Under the table?”  She asked curiously, breaking role.</p><p>Jake held her hand, “Claire.”  He gave her a look and smiled reassuringly.</p><p>“Sorry, sorry.”  She grinned and knelt down, crawling under the table and wiggling her bottom at Jake, receiving a playful swat in return.  As she turned to lay on her back, he was under the table and crawling over her swiftly, his forearms resting on either side of her head as he lowered his face to hers.</p><p>“Naughty lasses deserve naughty treatment.”  He teased, his voice a low seductive groan.</p><p>Claire lifted her legs on either side of him to cradle his hips and he moved a hand down between them to guide himself inside of her with a quick hard thrust.  They both let out involuntary pleasured sounds.</p><p>“Have you been this wet the whole time I was away?”  He asked, watching her face as she let out a moan.</p><p>“Yes Captain!”  Claire gasped breathlessly as he thrust into her again roughly.</p><p>“Good girl.”</p><p>She moved her hands to the table legs, holding onto them tight as Jake rocked into her faster, arms cradling her head.  Claire lifted her legs higher around his thighs locking them tight, causing him to push deeper.  The table began to shake from their movement and she put her head back with a sharp cry.  Jake looked up at her suddenly and grinned, pleased with himself.</p><p>“New move, ya like it?”</p><p>“Oh God yeah, don’t stop!”  She closed her eyes tight, letting out louder cries as he pushed hard into her and then pulled out slightly, pushing in deeper.</p><p>“Claire,” Jake panted, “Put your arms around me.”  She moved her arms around his underarms and up his back holding him close as he rode her, rocking them along the carpet.  His grunts grew harsher with every push, Claire’s own voice matching his.  She felt herself starting to approach a powerful orgasm and her legs held him tighter as she gripped his neck.</p><p>“Fuck!  Don’t stop!”  She cried roughly.</p><p>“Shit!”  Jake gasped as he felt his cock jerk suddenly at her words.  “Ah shit!”</p><p>“Jake!”  She mewled, her nails digging into his shoulders.</p><p>Jake suddenly thrust into her and held still letting out a garbled cry against her neck as his release hit him hard.  Claire followed soon after, her own orgasm causing her to let out a long wail as she gripped onto him, riding him as best she could under his still body.</p><p>She slowed and felt him breathing hard against her as she stroked the nail marks on his shoulder soothingly.</p><p>“Thank you Captain.”  She murmured, kissing his collarbone.</p><p>“Oh shit, lady.”  Jake swallowed hard and took a breath, “You are one hot wench.”</p><p>Claire smiled and patted his back.  She wiggled under Jake’s weight and he pulled out of her delicately and rolled over pulling her with him into the crook of his arm.</p><p>“I need to go in the brig more often.”  She sighed against him.  “I think Pirate Jake is my favorite.”</p><p>“Me too, lass.”  Jake kissed her forehead with a euphoric sounding chuckle.</p><p>“So Captain, when you do leave port again?”  Claire leaned up on her elbow, running her hand along Jake’s belly.</p><p>“Not til much later.  Already looking for more Pirate Jake?”</p><p>“Always.”</p>
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